Inspiring Conversations with Rome Whittemore of Rome Khalil

Today we’d like to introduce you to Rome Whittemore.

Hi Rome, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
I. was born Cassandra, but from a young age I knew something didn’t line up between how I felt inside and what I saw in the mirror. I didn’t have the words for it back then, so I buried myself in sports and tried to blend in. I also knew early on that I was attracted to women, which caused a lot of tension at home. When my mom found out about my first relationship, she kicked me out, and that really shaped the way I hid parts of myself for years.

I eventually left home, but life didn’t get easier right away. I went through an abusive relationship, and joining the Army in 2007 became a way to escape and rebuild. Even under “Don’t Ask, Don’t Tell,” I was openly lesbian, and thankfully my battalion accepted me. After leaving the military, I became a parent and started building a new life, but I was still avoiding the deeper truth about who I was.

Everything changed when my mom passed away in 2017. In her final days, she apologized for not supporting me more. That stuck with me. I didn’t want to live with regrets, especially not while raising a daughter who deserves to see her parent living authentically.

Not long after, I discovered binders and the concept of being transgender, and it was like someone finally gave me the language for what I’d been feeling my whole life. The first time I put on a binder, I saw myself clearly for the first time. From there, I started therapy, began hormones in 2018, had top surgery later that year, and eventually began bottom surgery in 2020.

Since then, I’ve made it a mission to show up for others the way I needed when I was younger. I speak to college classes, school boards, and wherever I’m invited to share my experience. I work at TikTok, and do my best to help create more inclusive workplaces. .

Today, I’m a father, an OEF veteran, and a proud Black, white, transgender man. And for the first time in my life, I feel exactly like myself.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
It definitely hasn’t all been smooth. Being kicked out by my mom and living in a tent as a teenager was one of the hardest moments of my life, and it shaped a lot of the fear I carried for years. But when it comes to my actual transition, I’ve been fortunate in many ways. In the transgender community, people often talk about being “passing,” and that has helped me avoid some of the hostility many others face.

I’ve also been lucky to have insurance that covers a large part of my medical transition, though the financial side is still a major challenge. Bottom surgery alone has cost around $500,000, top surgery was $60,000, and testosterone runs about $70 every three months. And that’s not even counting things like electrolysis, which insurance doesn’t cover at all. So while I’m grateful, the expenses are still very real, and at times overwhelming. But I refuse to give up on becoming fully myself.

Right now, one of my biggest struggles is updating my birth certificate to reflect my correct sex. Arizona currently has a hold on birth certificate changes, and navigating that—especially with shifting political leadership—has been incredibly stressful. It feels like I’m always racing a deadline. But like every other challenge I’ve faced, I’m determined to see it through.

Thanks – so what else should our readers know about Rome Khalil?
My brand is really just me—Rome Khalil Whittemore. I’m an advocate and public speaker focused on supporting transgender individuals and educating the communities around them. Whether it’s in workplaces, schools, on social media, or out in public, I show up wherever I’m needed. It’s funny, because I used to be terrified of public speaking and even struggled to feel comfortable in the LGBTQIA+ community. Everything changed when I finally embraced who I am. Finding my identity gave me the courage to use my voice.

What I’m most proud of is the visibility I provide. I get the opportunity to speak in classrooms, at events, and in community spaces, and every time I do, I think about the people who don’t have support at home or in their everyday lives. I want them to know they’re not alone. I’ve had students reach out to me through Instagram, and I make it a point to check in on them. I even give them a phone number that comes directly to me because sometimes a real conversation in a hard moment can prevent a crisis, maybe even save a life. When someone reaches out, they’re not getting a call center or someone who doesn’t understand. They’re getting someone who’s lived it.

I’m here for everyone. Trans individuals, allies, families, friends. A transition isn’t something one person goes through; it affects the whole circle around them in different ways. That’s why my work isn’t a typical “business.” No one is just a client or an opportunity. This is deeply personal. It’s passion-driven, people-centered, and rooted in real human connection. My goal is simple: To make sure everyone I encounter feels seen, heard, and supported.

Before we let you go, we’ve got to ask if you have any advice for those who are just starting out?
If I could offer one piece of advice to anyone just starting out, whether that’s in their transition, in advocacy, or simply in figuring out who they are, it would be this: Take your time, trust yourself, and don’t let fear convince you that you’re alone. I spent so many years hiding parts of myself because I was afraid of disappointing people or losing them. Looking back, I wish I’d known that living authentically doesn’t push the right people away, it brings the right people in.

I also wish someone had told me that it’s okay not to have all the answers at the beginning. Transitioning isn’t a race. It’s a series of moments where you learn, grow, and become more of who you’ve always been. Ask questions. Reach out for support. And don’t be afraid to take that first step, even if it feels small. My own journey didn’t start with a big decision, it started with a binder I ordered online and the courage to look in the mirror and say, “This feels like me.”

Another thing I wish I’d understood earlier is that transition doesn’t just affect you, it affects the people around you too. Give them grace where you can, set boundaries where you need to, and remember that their journey isn’t a reflection of your worth. You deserve to be seen and respected exactly as you are.

Most importantly, find community. Whether it’s online, at school, at work, or through advocacy groups, community can be the difference between surviving and thriving. If you ever feel like you don’t have someone, reach out. Message someone. Ask questions. There are people, myself included, who genuinely want to support you.

And finally, don’t give up. There will be hard days, confusing days, expensive days, and days when everything feels like it’s on hold. But there will also be days where you look in the mirror and recognize yourself, days where you feel free.
Those moments make every step worth it.

You’re not alone, and you don’t have to do this perfectly. Just do it authentically.

Pricing:

• $0 – Elementary Schools (bullying prevention)
• $200 Per class- Jr. High and Colleges.
• $300 – Public Events ( Flat Rate)
• Variable Rate – Workplaces ( Starts at $500)
• Prices are subject to change based on needs/requirements.

Contact Info:

• LinkedIn: https://www.linkedin.com/in/romekhalil
• Email: Romekhalil@myself.com
• Phone: 623-562-6819